Structural transformations in the international economy and the restructuring of work have made the transition from education to employment increasingly problematic. School-to-work pathways have become more socially segmented and the risk of under-employment and joblessness has increased for both vocationally and academically educated youth. Continuous passages have become less common and have given way to multiple entries and exits between schooling and working, under-employment, unemployment and domestic work. This edited volume of empirical studies is based on a series of comparable longitudinal research projects which draw on survey and biographical data from important players in the international economy, the USA, Great Britain, Canada and Germany. The studies document that social and gender inequality is a persistent structural feature that restricts the possibilities to take advantage of educational opportunities and career options. Furthermore, different institutional arrangements are shown to play a crucial role in distributing transition opportunities in a more equal way.